I started this post when I was 38 weeks pregnant and needed something to occupy my mind (besides the endless list of unpleasant side effects of being great with child). I never published it because I thought people would think I was insane for writing it in the first place and I didn’t think anyone would read it.
My how times have changed!
Now we’re all quarantined for Coronavirus and we have enough time on our hands that maybe a few people will be bored enough to read this admittedly ridiculous post. And…Taylor Swift is the topic I get asked to write about more than any other topic. So I’m giving the people (all five of you) what they want! Full disclosure: this list does not contain “Christmas Tree Farm” or “Only the Young” because they were released after I wrote it and I was NOT about to go back and re-do all the numbers. But I can sum up my thoughts by saying: Christmas Tree Farm slaps, Only the Young does not.
Some items of note:
-Cover songs & songs released by other artists are not included
-Taylor’s age when writing the song was taken into heavy account when ranking
-I like country music/singer-songwriter music better than pop, which influences the rankings
128.Girl At Home: I cannot come up with one positive thing to say about this song, which is why it ranks last. The entire premise is annoying. A guy wanted to cheat with her and she said no. Based on the lyrics, she thought this made her a feminist hero. It did not. I still cringe at the clunky “I know I don’t know her but I feel a responsibility to do what’s upstanding and right.” When it comes to the Taylor Swift discography – in the immortal memes of Mariah Carey – I don’t know her.
127.I Heart ?:This was released on the “Beautiful Eyes” EP exclusively for Wal-Mart in 2008. And you know what? Wal-Mart deserved better. Even at the time, when I was positively guzzling the Taylor Swift Kool-Aid, I didn’t understand the point of this song. It doesn’t make any more sense in hindsight. It’s supposed to upset a guy who did her wrong that she has “I Heart ?” written on her hand. Yeah…I have a lot of question marks, too.
126.Christmas Must Be Something More: Listen…I think Christmas means something more. But this song is preachy nonsense. I’ll take my Yuletide sermons from The Grinch and The Muppets, thank you very much.
125.Beautiful Eyes: Another Wal-Mart EP release. Because Swift is such a prolific songwriter, even her duds aren’t bad, per se. This track is simply irrelevant in comparison with some of the other stuff she wrote at this age.
124.Stay Beautiful: I never could get into this one. Yet another song about pining away for a guy who just doesn’t know she’s been there all along. I have no problem with that theme (see You Belong With Me), but this one never gets off the ground lyrically.
123.Speak Now: The theme of the Speak Now album is derived from the phrase in a traditional wedding ceremony, “Speak now or forever hold your peace.” The premise is: it’s better to say how you feel and risk the results than it is to sit in silence and let your chance go by forever. Unfortunately, this title track does not capture that sentiment. It’s awkward and contrived. Speak Now is such a triumph as a whole, which is why this song sticks out as particularly bad for me.
122.Gorgeous: I want to like this song. I’m happy that Taylor is happy. But the lyrics leave so much to be desired. I mean I really can’t say much for the sad/mad rhyming in the bridge and the monotony of the verses. She has spoiled me to the point that I expect more from her.
121.Superman: This bonus track from Speak Now is about seeing your man as a hero, even if he’s just walking out the door to go to work. That’s a wonderful premise. Below the surface, it’s about a relationship that is absolutely toxic. Swift hopes he doesn’t “save some other girl,” and says she’ll be waiting for him on the ground, wishing he would call. We can surmise through context clues that this song is about John Mayer, which adds a whole ‘nother level of cringe.
120.Innocent: This was written about the Kanye situation. I guess I should specify…the original Kanye situation, when he stole the mic from Taylor at the VMA’s and declared Beyoncé’s video the greatest video of all time. It features poignant lyrics and an almost haunting melody, but feels just a teensy bit gratuitous given that Kanye didn’t, like, murder anyone. His subsequent behavior feels more deserving of a strong response than his original offense. Also, while I have the microphone, Beyoncé doesn’t need Kanye to advocate for her. She’s Beyoncé.
119.A Place In This World: This one gets some pity points for being one of the first songs Swift ever wrote. She was just a kid, after all, which explains why this track doesn’t say much of anything. Although…there are people (or should I say men?) on country radio right now who couldn’t write this song now, much less as a child.
118.False God: Hozier’s “Take Me To Church” already did what this song was trying to do and did it better. Also, I am completely creeped out by songs that equate sex with religion. Not today, Satan.
117.The Moment I Knew: Taylor Swift has an uncanny ability to make her experiences feel universal, no matter how many personal details she shares. However, the hyper-specificity of heartbreak resulting from the realization that your relationship is over because your boyfriend didn’t show up to your birthday party after he said he would be there is too much for even her abilities.
116.The Outside: Another one of Swift’s first songs. This one is about feeling left out by girls at school. A bit redundant alongside “A Place in This World,” I rank this one the higher of the two because it has a clearer narrative.
115.Call It What You Want: I’m so glad Taylor is at a place in her life where she doesn’t care what people say about her relationship, she’s happy, and she has boundaries in place to allow her to keep some things for herself. I just did not connect with this song. I find the bridge where she answers her own question (Would you run away with me…yes) annoying. I feel bad even saying that because I really am happy for her and I want her to feel the way this song describes. It just didn’t do anything for me personally.
114.Sweeter Than Fiction: I have a love/hate relationship with the songs Taylor does with Jack Antonoff. This one leans closer to hate. I forgot it immediately after listening to it the first time. It struck me as clunky and over-produced. But he also gave us Out of the Woods, so it’s hard to be that upset.
113.Starlight: Taylor has been known to be quite the revisionist historian (she once gave an interview where she claimed “Style” was inspired by the timelessness of certain fashion trends), and she takes several liberties with this fantasized account of how Ethel Kennedy met Bobby Kennedy. I’m just not a huge Kennedy family fan, so I’m not prepared to dance to a song about their matriarch’s fictionalized love story. *shrug emoji*
112.King Of My Heart: Again, I couldn’t be happier for Taylor. I don’t care for the chorus on this one and overall it’s a bit too electronic for my taste. An honorable mention for the line: “Is this the end of all the endings?”
111.Superstar: This song has a beautiful melody, but I am just not a fan of the subject matter. It’s about being in love with a celebrity and knowing they’ll never know who you are. I mean…we can all relate, but I’m not sure we need to sing about it. The chorus gets stuck in my head sometimes in spite of myself, which is a testament to Taylor’s ability to craft the perfect earworm.
110.Christmases When You Were Mine: Leave it to Taylor Swift, The Patron Saint of Breakups, to provide us with a song that laments feeling lonely at Christmastime. If you’ve never been broken up with during the holidays, perhaps you can’t appreciate how deeply it sucks. But let me assure you from personal experience, it definitely feels like something there should be a Taylor Swift song about.
109.A Perfectly Good Heart: A bonus track from her debut. There’s nothing wrong with this song, but there’s nothing great about it either. Of course, if you were a recently heartbroken teenage girl circa 2006, this song was required listening.
108.Tied Together With a Smile: Written about a girl Taylor knew in school who struggled with bulimia, this one struggles a bit in the verses. But the chorus is so good I can’t rank it any lower.
107.I’m Only Me When I’m With You: A cute bonus track about feeling understood in a relationship. It’s an encapsulation of what it’s like to be young, when we all feel like no one understands us except our friends. I loved this song when it came out; but it’s not one I go back to like some of her other early tracks. It also gets knocked a few slots for production that sounds like it was recorded in an abandoned barn, which I think it sort of was.
106.You Need To Calm Down: I always respected that Taylor wanted to keep her politics to herself. I never understood the backlash she got for that. I also respect that we all grow and change over time, and she is now at a place where she wants to use her platform in that arena. It does, however, feel a leeeeeetle bit much to go from being completely silent on all things political to literally telling people who to vote for and endorsing federal legislation. Like, I have whiplash from just typing that. It’s a fun song that makes some good points. I’ll stop there because the internet is a scary place for discussing politics.
105.The Lucky One: Ah, the classic “fame sucks” lament that every artist eventually puts out if their career lasts long enough. I loved the aesthetic of the Red album so much, and this just didn’t fit with that vibe. I must give credit, though, for the lyric: “And your lover in the foyer doesn’t even know you.”
104.Picture To Burn: Two tracks in on her first album and Taylor was already showing us she could serve up a revenge track ice cold. Dripping with sass, this song perfectly captures the bratty emotions of high school heartbreak. What Southern girl didn’t want to scream “You’re a redneck heartbreak who’s really bad at lying” at her cheating boyfriend? You’re not likely to hear this one now if Swift has anything to say about it. Its politically incorrect original lyrics have made it a song she refuses to perform.
103.Welcome To New York: Eventually everyone who moves to NYC succumbs to the Stockholm Syndrome of the place. This song gave us a wealth of Instagram captions for our trips to New York. As the 1989 opener, it also brought to life the 80’s synth sound Taylor was exploring on her first official foray into pop. I could take this song or leave it, especially in comparison with some of the other songs on 1989.
102.Mean: For reasons unclear to anyone but Taylor, there was a time when she was fixated on the negative feedback of one particular critic. I won’t name him here because he’s gotten enough attention. This song was a direct response to his negative reviews. It’s hard not to love an anti-bullying anthem set to banjo, but the bridge is a bit harsh. Swift calls him “pathetic and alone in life.” At the time she released this song that felt like a sick burn. Now it just feels, well…mean.
101.Better Than Revenge: This is probably one of those songs Taylor should have written but never released. It’s objectively a good song, with major Paramore energy that sees Swift embrace delicious, villainous pettiness. It’s everything you want to say to the girl your boyfriend left you for, but saying it out loud in front of the whole world is not ideal. Add to that the fact that Swift performed this on tour complete with faux slapping her backup singer across the face and you get a big fat yikes. ALSO, this song is on the same album as “Mean.” Irony abounds.
100.Bad Blood: In the same vein as Better Than Revenge, this song was about a personal vendetta and ended up playing right into the media trope that women are catty rivals. The songwriting once again shines on the bridge, however. “Band-aids don’t fix bullet holes. You say sorry just for show. If you live like that, you live with ghosts…If you love like that blood runs cold.” A chilling lyric, indeed.
99.Look What You Made Me Do: There’s a lot about this song that I respect. The fact that it was such a MOMENT in pop music, the genius of sampling perhaps the wormiest earworm of all time (Right Said Fred’s “I’m Too Sexy”), the fact that she finally played the villain and not the victim…I could go on. But what attracts me to Taylor’s music is the lyrics, and this song doesn’t deliver in that arena for me. But of course, Taylor is incapable of writing a song without at least one lyrical nugget. Here they’re “Honey, I rose up from the dead, I do it all the time!” and “I don’t trust nobody and nobody trusts me. I’ll be the actress starring in your bad dreams.” P.S. my feelings are still hurt from seeing all the Old Taylors falling down in the music video.
98.Eyes Open: I rank this one higher than a lot of songs I listen to more often because it demonstrates Taylor’s ability to extract a narrative even when she hasn’t lived it. Commissioned to write for the Hunger Games movie soundtrack, she penned this from Katniss’ perspective in the arena.
97.The Man: This song makes all the points and it couldn’t be more well-timed. I don’t rank it super high because I don’t want to listen to it over and over. It’s a bummer how true the lyrics are, especially in the music industry.
96.Wonderland: This 1989 bonus track compares a tumultuous relationship (i.e. Haylor) to a fall down the proverbial rabbit hole. As Taylor notes, “It’s all fun and games ‘til somebody loses their mind.” The song feels very dissonant and frantic, emphasizing the meaning of the lyrics.
95.London Boy: In spite of the fact that this sounds like if the EPCOT U.K. pavilion wrote a song, I like it. As a totally basic Anglophile, it speaks to me. Critics have been hard on it but Ryan Tedder said it’s one of his favorites so…critics who?
94.Red: I always say I don’t like this song, but every time I go back to the Red album (every fall, obviously), I have to admit it’s a banger. For me, this is one of the few Taylor Swift songs where the production/performance value outshines the lyrics.
93.Stay Stay Stay: The secret message (oh, how I miss those days) in the album liner for this song is, “Daydreaming about real love.” We can therefore presume it’s not about anyone in particular. But I like to imagine Taylor listening to this song now and realizing it was about her current relationship, she just didn’t know it at the time. One thing I love about Taylor’s music catalog is you could make a playlist of the saddest breakup songs or the happiest, bounciest songs with equal ease. Stay Stay Stay is most definitely on the bouncy playlist.
92.Never Grow Up: This song features one of the saddest lyrics I have ever heard: “I just realized everything I have is someday gonna be gone.” SHEESH. Taylor wrote this song after moving out on her own and it reflects beautifully on the fleeting nature of childhood. I don’t tend to go back to this song much because it’s so very sad.
91.Change: This victory anthem was written after Swift’s first big wins during awards season and ended up being the Olympic theme for Team USA. There’s not all that much to say about this one, but it ranks above others I like for the sole fact that it shows off how freakishly long Taylor can hold out a note.
90.I Forgot That You Existed: I’m a little bummed about all the songs Taylor has written about Kanye West. I’m sad that he took up that much space in her life. Hopefully, this is the last one we’ll ever hear, because it’s the ultimate kiss off. Broadly, it applies to the moment you realize you’ve stopped giving a toxic person power in your life—and it no longer takes effort. “It isn’t love, it isn’t hate, it’s just indifference.” I wish you all the freedom of that moment with the toxic people in your lives. (Lord knows we all have them.)
89.I Wish You Would: This Jack Antonoff track has a little too much going on for me, but it features Taylor at peak pop star vocals so things even out. The lyrics feature things we probably all wish we could say to a lost love in those weak moments when we want them back.
88.Dancing With Our Hands Tied: This song gives us a glimpse into what it’s like to have a relationship in the public eye. Taylor had all but decided she would have to be alone as the scrutiny surrounding her relationships seemed to make them impossible to manage. But then she fooled around and fell in love. I wish this was a little more ballad and a little less bass drop, but I do appreciate the glimpse into her world provided by the lyrics.
87.ME!: It can’t be overstated how much Taylor loves an emo moment. So it makes total sense that she would work with Brendon Urie of Panic at the Disco! fame. But…plot twist! They teamed up for the happiest little self-love anthem you’ve ever gotten a spelling lesson from. I love the juxtaposition of the lyrics “And there’s a lot of cool chicks out there/And there’s a lot of lame guys out there.” Ain’t it the truth?
86.How You Get The Girl: I seem to recall Taylor saying in interviews during 1989 press that this song contains the instructions you should follow if you want to win back a girl you did wrong. This sweet-as-cotton-candy track, like the wispy treat, is best enjoyed sparingly-but it sure is fun from time to time.
85.New Romantics: Clearly influenced by her life in New York, this strikes me as the modern version of something F. Scott Fitzgerald might have written about the 1920’s. I realize that’s an extremely bold statement, but it’s about navigating a social landscape that is completely of its time. If I were still in college I would write an essay about this parallel. This is another that’s chock full of one liners Swift had surely been sitting on like, “Cause baby I could build a castle out of all the bricks they threw at me.” Another honorable mention: “The rumors are terrible and cruel, but, honey, most of them are true.”
84.I Don’t Wanna Live Forever: I want to rank this lower because I have so much distaste for Zayn and Fifty Shades of Grey. But I love the bridge, Lord help me! It would be hard for anyone to keep up with Zayn vocally, though it pains me to admit it, but Taylor delivers.
83.Dress: I mean…what to say about this song that I’m comfortable publishing on the internet? I think what separates this from other *sexy* songs of this era is that it highlights the intimacy of being known and accepted even at your worst by your significant other. I honestly can’t believe no one beat her to this hook, but then again of course they didn’t. She thinks our thoughts before we think them, y’all!
82.I’d Lie: I would have taken this on the debut album in a heartbeat before A Place in This World, The Outside, or Stay Beautiful. This is one of my favorite early Taylor songs and it’s a crying shame it was relegated to the Walmart EP. This is an early example of Swift’s ability to include hyper-specific detail (“…born on the 17th”) and yet somehow make the lyrics feel totally universal at the same time. “First thought when I wake up is, ‘My God, he’s beautiful.’ So I put on my makeup, and pray for a miracle.” Who can’t relate to that…especially in high school?
81.So It Goes: My vanilla, conservative self is a bit scandalized by this song, but I love the production. And the bridge, as so many of her bridges, goes OFF. I do take issue with the lyric, “I’m so chill but you make me jealous.” I love her dearly, but if anyone on this planet has no chill, it’s Taylor Swift.
80.Come In With The Rain: A lovely ballad with profound lyrics like, “I’ve got you down, I know you by heart. And you don’t even know where I start.” This bonus track from Fearless: Deluxe Edition is fairly simple but packs a punch.
79.Tell Me Why: A Fearless deep cut that sees Swift finally telling off a person who insists on keeping her down. This song contains one of my favorite lyrical asides: “And here’s to you and your temper, Yes I remember what you said last night.”
78.The Best Day: This is a lovely tribute to Taylor’s mom. The last chorus always gives me chills. I’m pretty sure if you listen to this and “Soon You’ll Get Better” back to back, you’ll turn into Sadness from Inside Out.
77.Miss Americana And The Heartbreak Prince: Taylor swears this song is a political commentary. I don’t think the song makes a ton of sense regardless of how you look at it, but as the kids say, it’s a vibe.
76.Invisible: Though lyrically a bit simplistic compared to some of her other ballads, this song captures the big, big feelings of watching the boy you like date someone else. This appears to be something Taylor experienced a lot of in her time, which could be why I latched on to her music so tightly. Ya girl knew a thing or two about unrequited love, and no one articulates it better than Ms. Swift.
75.Mary’s Song (Oh My My My): A sweet storyline inspired by Swift’s elderly neighbors, this song has aged well. If you want to feel all warm and fuzzy inside or need a song to play at your grandparents’ 50th anniversary party, might I recommend this track? The fact that this was never a single upsets me to this day.
74.Should’ve Said No: This song showcases some of Taylor’s best early vocals. If you’ve ever been cheated on and you haven’t scream-cried to this song…you’re lying. This song also represented a *moment* in Swift’s career. It was given the honor of a rain performance and played at some of her earliest award show appearances. This is not a song I tend to go back to, but whenever I hear it, I must say it holds up well.
73.Hey Stephen: Who knew so many words rhymed with Stephen? One of several songs where Taylor names names, this one details a meet-cute that left her daydreaming about a future with the Stephen in question. This track is sweet as sugar, and I’m a sucker for any song that includes a well-placed giggle. It also has several stand-out lyrical moments, including, “All those other girls, well, they’re beautiful, but would they write a song for you?” We know as well as Stephen that the answer is no.
72.It’s nice to have a friend: The production on this one is so interesting and soothing. It really evokes the feeling of simple companionship talked about in the song. I like the linear imagery of an easy childhood friendship, a friendship that blossoms into romance, and ultimately enjoying friendship with a spouse.
71.Getaway Car: Finally, a peek inside what in the actual heck was going on in her mind during Hiddleswift. Don’t get me wrong, Tom Hiddleston is attractive, but even as a diehard fan I remember thinking “What is she doing?!” As it turns out, she needed a reason to leave Calvin Harris, just as everyone who has ever dated a professional DJ eventually needs a reason to leave them. She uses a sort of Bonnie and Clyde metaphor to describe a doomed relationship that was only ever meant to be a diversion. If you’d like a visual aid to go with this song, I suggest googling paparazzi photos of Taylor and Tom in Italy, where it is abundantly clear on her face that nothing good starts in a getaway car.
70.Today Was A Fairytale: There is a substantial amount of hate for this song within the fandom, but it’s my party and I’ll stick up for underappreciated soundtrack songs if I want to. I think seeing the magic in everyday life is a hallmark of Taylor’s songwriting and it’s a tenet of my worldview, so Today Was a Fairytale forever! This song was the cornerstone of the soundtrack for Garry Marshall’s “Valentine’s Day.” Her vocals are gorgeous, the lyrics are sweet, the haters gonna hate.
69.The Way I Loved You: Sigh…the lure of the bad boy. If you’ve ever been guilty of thinking that drama = love, this one’s for you. With a breathless head rush of a chorus, narrative verses, and a driving bridge, this one is a standout on an album of pretty much all standouts.
68.End Game: In case you ever wondered if Taylor Swift could write rap, the answer is yes. “And I bury hatchets but I keep maps of where I put them” would be at home on any hip hop chart topper. She also serves us sultry power vocals and cheeky winks at the camera like “I swear I don’t love the drama…it loves me.”
67.Ready For It?: As I just mentioned, Taylor Swift can rap. Who knew? There will never be a bigger flex than “He can be my jailer, Burton to this Taylor.” Now…when are we gonna get that Drake collab?
66.Shake It Off: I loved this song so much when it came out, I made it my alarm. Consequently, I am now #triggered every time I hear it. But I will still never be over the bridge. And I maintain that “the fella over there with the hella good hair” is Harry Styles.
65.Daylight: When I heard “I once believed love would be burning red, but it’s golden,” I was shooketh. I don’t *love* ending an album with a voice memo, but the line “you are what you love” made sense to wrap up an album titled, “Lover.”
64.Crazier: Don’t @ me, but these are some of Taylor’s best vocals ever. What a travesty that they appear on the Hannah Montana movie soundtrack of all places. This is a sweet country slow dance that, in my opinion, didn’t get enough love from fans.
63.Sparks Fly: The Taylor Swift fandom is living proof that if you just b*tch and moan enough, eventually you will get your way. This song is Exhibit A. It was an unreleased track Taylor had only performed live, and fans essentially harassed her until she recorded a studio version. Another lyrical classic from the School of Swift Songwriting, it features kissing in the rain and a metaphorically significant staircase. This song loses it a little bit in the second verse for me, but the chorus goes so hard I don’t really care.
62.Untouchable: This is the only cover song to appear on this list. Swift gets songwriting credit for completely re-imagining the melody of this Luna Halo tune. Honestly, she did this song several favors. We can’t give her credit for the lyrics, but this may as well be a Taylor Swift song by the time she’s done with it.
61.You’re Not Sorry: Taylor has evidently met a lot of toxic people in her time. This song describes the moment you decide you’re done with a person who apologizes over and over but keeps hurting you. As always, she is well beyond her years here in terms of emotional maturity.
60.The Story Of Us: That awkward moment when you dated John Mayer and it ended badly (does any relationship with John Mayer end well?) and then you’re seated near each other at an award show. We’ve all been there, amirite? Despite the inspiration behind this song being something none of us will ever experience, Swift works her magic and spins a narrative we can all relate to. She serves up major Shania Twain vibes with the sassy spoken transitions (“Next chapter…”). This song is chock full of impactful one-liners that describe what it’s like to watch the story of a relationship change so drastically from what you thought it would be. Among my favorites? “But you held your pride like you should have held me.”
59.Death By A Thousand Cuts: Mmmkay, full disclosure: the phrase death by a thousand cuts doesn’t super resonate with me. But this mega-bridge cannot be denied. (Her heart. Her hips. Her body. HER LOVE.) Thank God she can still write a breakup song. I may be happily married but we all have feelings to feel!
58.Jump Then Fall: This first track from Fearless: Platinum Edition fits perfectly with the rest of the album’s themes. Young love, jumping into a relationship without fear, and Being Extremely Cute…all elements of the Fearless Era. The dreamy verses and lilting chorus are full of lyrical gold nuggets like, “I had time to think it o-over, and all I can say is come closer.” If you can listen to this song and not smile, you might be broken.
57.All you had to do was stay: Inspired by a dream, this pop anthem is a big sorry ‘bout it to an ex who wants you back when THEY’RE THE ONE who let you go. I love the lyrics in the pre-chorus “People like you always want back the love they gave away, and people like me wanna believe you when you say you’ve changed. People like you always want back the love they pushed aside, but people like me are gone forever when you say goodbye.” You tell him, Taylor.
56.I think he knows: When the relationship is so on you don’t even have to define the relationship. Despite the fact that I could not for the life of me understand the lyric “I want you bless my soul” and FULLY believed it was “I want you, that’s my toe.” and was baffled as I have never been baffled in my life, this song grows and grows on me. Let’s all sing together: LyricalsmileindigoeyeshandonmythighwecanfollowthesparksI’lldrive.
55.You are in love: If I practice cognitive dissonance and willfully forget that this was inspired by Lena Dunham and Jack Antonoff, two people whose relationship I would like to know absolutely nothing about, this one is in my top tier of her love songs. I love the quiet pulsing–the imagery of those seemingly mundane and yet in hindsight huge and defining moments in a relationship. There’s also a pretty defining Swift lyric in the bridge, “And you understand now why they lost their minds and fought the wars. And why I’ve spent my whole life trying to put it into words.” Also, the dancing- in-a- snowglobe lyric? We have to acknowledge that You Are in Love walked so Lover could run.
54.I Know Places: This is a song about Taylor realizing that any relationship she has is going to have to take place out of the public eye in order for it to survive. At least, that’s what she said during 1989 press. She went on to put us through Calvin Harris and Tom Hiddleston so I’m not sure the lesson sunk in at the time. This song gets me in my feelings because I love her and Harry Styles and I feel like they just never got a CHANCE because there were so many eyes on their relationship. I don’t think they would be together today, but I do think they could have had a long relationship with an amicable breakup. (Or, if I’m being honest with myself, he would have habitually cheated on her with Victoria’s Secret models). But just think of the songs we’d be missing out on if it weren’t for all the turmoil.
53.Holy Ground: Part Three in the Joe Jonas Trilogy. Swift looks back on a relationship with the patina of time and hindsight and realizes it was good. There’s not a single low point in the lyrics, the driving beat is downright exhilarating, and she sings the crap out of it. A personal favorite moment? The way she attacks, “And I guess we fell apart in the usual way, and the story’s got dust on every page, But sometimes I wonder how you think about it now, And I see your face in every crowd.”
52.Treacherous: Poetic verses, a pretty chorus, and a bridge that could be a chorus make up this song about recognizing a relationship might be risky, but going for it anyway. A standout lyric: “And all we are is skin and bone; trained to get along. Forever going with the flow, but you’re friction.” If we got a whole album of this singer/songwriter vibe from Taylor I would die happy.
51.The Last Time: This duet with Gary Lightbody of Snow Patrol is immersive, understated, cinematic, and y’all have slept on it long enough. Honestly the entire Red album is so emotionally evocative for me (except Starlight and The Lucky One, boooooooo!). This is one I don’t hear a lot of fans talking about but I love it. So I guess as the kids would say I’m a “The Last Time” stan? Regardless of how you phrase it, if you see me in my car with this song turned up way too loud trying to sing both parts by myself…just mind your business.
50.Begin Again: The sweetest little almost-acoustic ballad about working up the courage to go on a first date after a bad relationship. For inquiring minds, this was inspired by a date with the lead singer of Parachute and I’m willing to bet “Kiss Me Slowly” is about this same date or a date thereafter. I love the sentiment of this song and it’s one of her many that we can all relate to. It’s SO hard to open yourself back up after being hurt. I love the hopefulness of this song. It feels like she’s laying down a weight she’s carried far too long and taking a deep breath.
49.We are never ever getting back together: Written as bubblegum pop as possible to piss off a Top 40-hating hipster ex, this song gives us new levels of pettiness to aspire to. (Or not aspire to? Don’t be petty unless it’s making you a lot of money.) One of my many obsessed fan opinions is that the voice memo in this talking about him calling her and saying “I still love you” is about the same phone call she references in All Too Well. That’s called GROWTH, girlies.
48.Long Live: A lot of Taylor Swift fans could take or leave this song, but I have a personal connection to it. I did a Cru summer mission working at Walt Disney World the summer after Speak Now came out, and all the fairytale references fit perfectly with my experience. You know those experiences where you live so much life with a group of people that you can’t really explain it to anyone who wasn’t there…kind like summer camp? This song is the anthem for those. So many of the lyrics are special to me, but the one that makes my heart flutter is, “Long live the walls we crashed through, how the kingdom lights shined just for me and you.” #emporiumforever
47.Afterglow: Thanks to Taylor, women now have an anthem for when they get into a needlessly huge fight with their partner because they were feeling a lot of things. I can think of so many arguments with Andrew that fit into the narrative of this song, where I made assumptions that then fueled my emotions without ever giving him a chance to explain himself. I love the heavy drums in this track and the line “This ultraviolet morning light.”
46.I Did Something Bad: I wish so badly this had been the opening single from Reputation. What Blank Space started, IDSB finished. Swift fights back against criticism surrounding her dating life with this banger she claims to have written from a character’s perspective. Personally, I think she was just being completely honest. The lyrics left me wondering, “Girl, did Tom Hiddleston spend your money?!” The production, the hand claps, the clap backs…who could ask for anything more?
45.New Year’s Day: Yet another example of an incredible lyric being tossed in as an outro: “Please don’t ever become a stranger whose laugh I could recognize anywhere.” This piano ballad sees Swift reflecting on having found a relationship that will weather the highs, the lows, and the mundane in between. Your love is not just by your side for the glitter and excitement of New Years’ Eve, they’re cleaning up after the party with you the next day. Ever the songwriter, she notices the poetic significance of this.
44.Delicate: The opening lines of this song knocked the wind out of me when I first listened. “This ain’t for the best. My reputation’s never been worse, so he must like me for me.” Wow. This prequel to Cornelia Street is full of all the hope and vulnerability of the beginning of a relationship, before it’s officially official. That stage when you realize you really like this person and you don’t want them to date anyone else but you aren’t sure if it’s too soon to say that. Well, you better believe Taylor Swift says it.
43.Cold As You: The fact that this song was co-written by a 15 year old is stunning. The lyric “So I start a fight cause I need to feel something, and you do what you want cause I’m not what you wanted” still slays me. The lyric about dying is the only reason this song doesn’t rank higher for me. It pushes it just a little too far over the top. But the emotional intelligence she displays here is truly impressive. If you’re a casual fan but have never listened to deep cuts from the debut, this is one to seek out.
42.Soon You’ll Get Better: The only reason this song and Ronan aren’t ranked higher is because I can’t really listen to them without getting depressed. They are both beautiful songs and there are people who need them. For those who don’t know, Taylor’s mom has been battling cancer for the last several years. This song, featuring fiddle and breathy harmonies from the Dixie Chicks because that’s her mom’s favorite band, gives us a glimpse into the private fears and grief Taylor has been carrying as her mom fights. There is nothing to critique about a song that so bravely and beautifully captures something so many can unfortunately relate to.
41.Ronan: I don’t know of another artist who could write this song. I’ve only listened to it once because it was so devastating, but I think about the lyrics often. The main charity Taylor works with is St. Jude. Through her work with childhood cancer, she found the story of a four year old boy named Ronan who died from a rare form of cancer called neuroblastoma. His mom kept a blog of their journey. Taylor was inspired by her words to write this song. She names Ronan’s mom as a cowriter, ensuring she would get a share of the royalties, and donated proceeds from the song to cancer research. I wish this song didn’t have to exist, but I have to imagine it captures the feelings of anyone who has lost a child to cancer. What a wonderful way to use your talent to impact those who need it most.
40.Haunted: Taylor Swift can do so many things well. Haunted sounds like it could be an Evanesence song. But no, it’s just Taylor, embracing her emo side. Pulsing violins create a frantic sound and Taylor’s aggressive vocal is fraught with emotion. In addition to her versatility, Taylor can also articulate emotion sonically as well as lyrically. Haunted is a prime example.
39.The Other Side Of The Door: Dare I say it? The ranting bridge to end all ranting bridges. Every Taylor trademark you could want is present and accounted for: waiting in the pouring rain, rocks tossed at a window, fighting hard and making up harder. This is a song about fighting with a guy and then wanting him to try and win you back. If only Elizabeth and Nick had this song, Annie and Hallie might never have been separated. (Thank you to anyone who appreciates that Parent Trap reference)
38.Cornelia Street: An instant classic from her latest album, Cornelia Street is the sequel to Delicate. The memories from the start of this relationship are so precious, she couldn’t bear to relive them if she ever lost this person. Those of us who have been lucky enough to find true love can relate to that. This song has one of my favorite lyrical couplets of hers, “Barefoot in the kitchen, Sacred new beginnings.”
37.Out of the woods: This is another Taylor Swift song that I have lain awake at night thinking about. You guys. It literally SOUNDS like being lost in the woods. I mean how? The whole second verse is amazing (the paper airplane necklace reference!!), and the bridge features lyrics both hyper-personal and universal, as is her genius. (I say hyper-personal because none of us have ever been in a snowmobile accident with Harry Styles.)
36.Back to December: Remember all those memes about how Taylor Swift should have a song called “Maybe I’m the problem”? (I won’t get into my feelings on the sexism of that because the internet is not large enough to contain them.) Well joke’s on them because she already did, and it was called “Back to December.” This was the first time Taylor apologized to a boy in a song. Taylor Lautner was real sweet to her, you guys, and she let him go. But at least he has this beautiful balled to remember her by, with lyrics like, “It turns out freedom ain’t nothing but missing you.”
35.Forever & Always: Every breakup needs a good emo moment (or several), and this was Taylor’s when Joe Jonas broke up with her quite unceremoniously over the phone. I detect a bit of Alanis Morissette energy in the line, “Did I say something way too honest? Made you run and hide like a scared little boy?” I can tell you right now that as a senior in high school who was ghosted by the boy she was dating (before ghosting was even a term) literally the week this album came out, this song spoke to me. Taylor would go on to record a piano version of the song that explores the lyrics as a devastating ballad rather than an angry romp. In either version, her songwriting shines.
34.Style: Yet another song that applies very specifically to Taylor’s life and yet manages to remain relatable. On the one hand, a song about dating Harry Styles and not being able to stop dating Harry Styles even when you’re not dating Harry Styles. On the other hand, a song about a relationship that always seems to have a place in your life, even when the two of you aren’t officially together. To be honest, now that I type it all out, both scenarios are equally relatable.
33.Teardrops on my guitar: There is only one word for this song in the TSwift canon: Iconic. Even if the song itself isn’t your favorite, it established so many distinct characteristics of Swift’s songwriting. She names names. She switches up the lyrics in the last chorus. It features an excellent use of the repeated opening/closing lyric. This song also demonstrates Taylor’s ability to magnify minutia sonically and lyrically to match the way it feels. The reality is, Drew was some scrub she had a brief crush on in the single year she actually attended high school. This song turns those feelings into an epic. If you’ve never watched her cover this on the Red tour, do yourself a favor and look it up now.
32.Our Song: Swift wrote this for her high school talent show. Let’s have a moment of silence for the self-esteem of the other performers. Our Song is a lyrically innovative story of young love at its sweetest. Lines like “When we’re on the phone and you talk real slow, ‘cause it’s late and your mama don’t know” provide the relatable emotional snapshots that are such a trademark of her songwriting. Just try to listen to this song without feeling like you’re 15 again.
31.Don’t Blame Me: Taylor tries her hand at “church choir but make it sexy” and dang it if she doesn’t knock it out of the park. I feel like because we had this song, we didn’t need False God. If you’re one of those people who still insists Taylor Swift can’t sing, please listen to this song and get back to me. Actually don’t get back to me. I don’t have room in my life for that kind of negativity.
30.Paper Rings: Add this one to your kitchen dance party playlist. I love the lyric “Honey, without all the exes, fights, and flaws, we wouldn’t be standing here so tall.” I want this song to soundtrack the next Drew Barrymore rom-com and I really can’t give a higher compliment than that.
29.If This Was a Movie: This bonus track from Speak Now has never gotten enough love. There has been some lyric confusion in the fandom surrounding Taylor’s lack of annunciation. How many Eli’s out there mistakenly thought this song could be about them? This song captures the sadness we feel when we realize it’s not going to work out like it does in the movies.
28.Ours: A bonus track that ended up taking on its own life as a single because it was just that good. The whole chorus is gold. Ours is one of many examples of Taylor sneaking heart-stopping lyrics in bubblegum songs. “Don’t you worry your pretty little mind, people throw rocks at things that shine.” You’d be hard pressed to find a lyric like that in anyone else’s bonus track.
27.Fifteen: “In your life you’ll do things greater than dating the boy on the football team. I didn’t know it at fifteen.” That’s just one of many impactful lyrics in this reflection on this tender age. Anyone who has ever been a fifteen year old girl has cried to this song. It’s true; all you want is to be wanted at that age. But there are bigger dreams out there for us all than fake love from high school boys. Thank God we have Taylor to remind us.
26.Fearless: This is a Taylor Swift song I go back to over and over. This whole album is so thematically perfect. It came out my senior year of high school and listening to it is like stepping into a time machine. Swift’s songwriting doesn’t always thrive on title tracks (see: Speak Now), but this song captures the essence of the album while also standing alone.
25.State of Grace: When you think arena rock, you probably don’t think Taylor Swift. And yet this song exists. She describes the beginning of a relationship as a state of grace, before anything has gotten messed up and everything is possible. This was truly a new sound for her at the time, making it a perfect opening track to Red. She fires off one-liner after one-liner with huge vocals surrounded by an immersive drum beat. “These are the hands of fate. You’re my Achilles heel. This is the golden age of something good, and right, and real.”
24.I knew you were trouble.: I will go to my grave swearing this song is about John Mayer. I think Miss Revisionist History puppeteer-d the narrative that it was about Harry Styles because it sold more albums. Or maybe it’s a Carly Simon “You’re So Vain” style roast of several guys. Who knows? Regardless of who it’s about, this was the song that solidified Taylor as a pop star.
23.Safe & Sound: Taylor Swift has served her fans just about everything we could ask for over the years, and with this song she served us spooky lullaby vibes. The macabre little weirdo in me could not love creepy Taylor more. The harmonies created by The Civil Wars only enhance the goosebump factor. This was another track she did for the Hunger Games soundtrack (See: Eyes Open) when asked to imagine the lullaby Katniss might have sung to Rue in the arena.
22.22: I agonized for longer than I care to admit over these rankings, but when I saw that 22 had ended up ranked number 22 without me trying, I knew I was done. This song came out the year I turned 22, my senior year of college. I lived with three of my best friends. For each of our birthdays, we were woken up by a dance party to this song. The amount of love and nostalgia I feel for this song is hard to measure. In addition to having a personal meaning, this song just nails what it’s like to be in your early 20’s. It is, in fact, miserable and magical, oh yeah. This is a Taylor Swift song that became a cultural *thing.* Everyone who has turned 22 since it came out has referenced it in some way, even Harry Styles himself.
21.Wildest Dreams: Even when she’s a cynic about love, Taylor can still write the heck out of a song. The pounding of Swift’s own heartbeat anchors this mournful yet resigned reflection on the fact that almost all relationships end. With lyrics like, “Someday when you leave me, I bet these memories follow you around,” this is one of the few Swift songs that doesn’t end on a hopeful note.
20.Come Back…Be Here: This is a bonus track buried deep on the Deluxe Edition of Red. It’s a long distance relationship theme song. More specifically, it’s about realizing you’ve fallen for someone after they’re gone. It’s also the first time she used the word “delicate” to describe the beginning of a relationship. So basically Come Back…Be Here walked so Delicate could run.
19.The Archer: This is Taylor Swift at her most self-aware, and consequently her most vulnerable. Her vocals blanketed by synth and vocoder, she sings “Who could ever leave me darling—but who could stay?” There’s a lyrical juxtaposition between this song and New Year’s Day, the album closer on reputation that I love. In the first bridge of NYD, she sings “Hold on to the memories, they will hold onto you. And I will hold onto you.” In The Archer, she sings at the end of both verses, “Help me hold onto you.” It’s so interesting to hear her acknowledge that she maybe doesn’t know how to be in a good relationship. We can all have a tendency to self-sabotage. And now we have a Taylor Swift song about it.
18.Sad Beautiful Tragic: As much as I love “22,” “I Knew You Were Trouble,” and “We are never ever getting back together,” there’s part of me that wishes Red had been all ballads and singer/songwriter acoustics. Part of the reason I wish that is because of this song. Taylor has a way of finding beauty in sadness. This song is about the moment in a breakup when you stop villainizing the other person and realize you two were just bad together. There were beautiful times that felt like magic, but for whatever reason the two of you could never get that back once it was gone. The lyrics are wonderfully brutal. “Words, how little they mean when you’re a little too late.” “You’ve got your demons and darling they all look like me.” “Hang up. Give up. For the life of us we can’t get back…” This song makes me wish I was sad even when I’m not.
17.Everything Has Changed: Here is another example of Taylor Swift just nonchalantly throwing in one of the best lyrics you’ve ever heard. In the outro she sings, “All I know is we said hello, so dust off your highest hopes.” She wrote this song with Ed Sheeran on a trampoline, and I don’t know a better way to describe it than to say it sounds like she wrote it with Ed Sheeran on a trampoline.
16.I Almost Do: In a catalog of highly relatable songs, this one might be the most relatable of all. Instead of calling an ex she knows she shouldn’t speak to anymore, she writes this song. If only we could all be so productive in our moments of weakness.
15.This Love: Over time, this track snuck up on me as one of my favorites from 1989. Taylor originally wrote this as a poem. It was produced by Nathan Chapman, who she worked with extensively on her country albums. It sounds like a siren song that might call out to you in a dream, with layers upon layers of restrained vocals. Seemingly built upon the old adage “If you love something let it go, if it comes back it’s yours,” the lyrics tell of a love she let go only to have it come back into her life right on time. “These hands had to let it go free and this love came back to me.” Poetry, indeed.
14.Enchanted: This might be the most Taylor Swift song there is. It honestly boggles the mind how she can take these tiny moments that we all experience, and blow them up lyrically and sonically to match how it felt to live them. Taylor meets a guy and thinks he’s cute and that they have a connection. Out of that we get this sweeping, cinematic masterpiece. There are sparkles and wonder and 2:00 am hoping…all the whimsical elements that make up our beloved TSwift.
13.Tim McGraw: The one that started it all. RIP to the careers that were killed when a 16 year old girl rode in on a song she wrote with Nashville veteran Liz Rose and it was this good. I’ll never forget hearing this for the first time in the car with my mom. We both stopped talking to listen to it all the way through. When we got home I Googled “Taylor Swift,” and the rest was history. A perfect country song, this track features a clear storyline and references Georgia, a Chevy truck, back roads, and God.
12.Breathe: Another song I go back to time and time again. This is such a poignant reflection about having to cut a person out of your life, but knowing they’re not a villain. I love the line, “Never wanted this, never want to see you hurt. Every little bump in the road I tried to swerve.” It’s been ten years since this album was released and every time I listen to this song may as well be the first time.
11.Blank Space: Taylor Swift saw your boyfriend slideshows and she raised you this irreverent bop. (For heaven’s sake, she did not date Zac Efron.) The day 1989 came out I had a hard time getting through the whole album because I just wanted to listen to this song over and over. Years later and I could still have it on repeat. I can’t pick one lyric to highlight because they’re all solid gold. And that pen click in the chorus? *chef’s kiss*
10.Cruel Summer: I didn’t know that Fall Out Boy Taylor was missing from my life until I heard Cruel Summer. Written as a Pete Wentz-style series of compelling imagery and jarring one-liners, this contains some of her boldest lyrics. “I love you, ain’t that the worst thing you’ve ever heard?” she shouts on a frantic bridge bookended by searing verses. I’m not sure but I think to drive around on a summer night with a car full of friends singing this as loudly as possible might be the law now.
9.Clean: If you have never gotten in your feelings in your car while it’s raining and this song plays in the background…have you even lived? Taylor teams up with delightful weirdo Imogen Heap to create a musical wonderland that describes what it feels like when you realize you’re finally over your ex(es).
8.You Belong With Me: If we were in a Ghost of Christmas Past style flashback of my life right now, we might look through the window of my hot pink bedroom and find an 18 year old Ashton performing the living hell out of this song in front of her dresser mirror. This is not just a song—it’s an anthem. Yet another example of Swift’s ability to include personal detail that feels universal.
7.Lover: With the sonic ambience of the last song played at a local dance in the 1960’s, Lover is Taylor’s greatest love song. I’ll never stopped being confused that she thinks leaving Christmas lights up until January is an act of rebellion, but that hardly matters in comparison with the rest of the lyrics. “My heart’s been borrowed and yours has been blue. All’s well that ends well to end up with you.” “And at every table, I’ll save you a seat.” She captures the cosmic coziness of true love.
6.White Horse: A breakup song that takes the fairytale theme and turns it on its head, with yet another reference to a stairwell. (Seriously, she loves stairs.) There are so many beautiful lyrics in this song, but the one I find most affecting is “This ain’t Hollywood, this is a small town. I was a dreamer before you went and let me down.” One of the things I love about Taylor’s breakup songs is they always end with a declaration of strength. In White Horse, she leaves that small town in the rearview to find bigger and better things. How is she so sad and yet so powerful?
5.Last Kiss: Undoubtedly one of the most devastating breakup songs ever written, Last Kiss features lyrics that silence even the loudest Swift skeptic. “So I’ll go sit on the floor wearing your clothes, All that I know is I don’t know how to be something you miss.” The entire bridge is so sad I can only describe it as emotionally indulgent. Like any Taylor Swift ballad, Last Kiss hurts so good.
4.Lovestory: Out of all her songs, this one is probably the most closely associated with Taylor by the world at large. It details a storybook love that feels timeless in any age. The lyrics ask us to believe that the fairytale love we dream about is real, even when it’s difficult. I don’t know her personally, but having listened to her most recent album, Lover, I have a feeling that sentiment rings more true now than ever for her.
3.Dear John: This song—and hear me out here— is one of the greatest acts of feminism in the last century. I don’t know if we can put audio in the Smithsonian but, if we can, I nominate Dear John. We all suffered watching human Lisa Frank kitten Taylor Swift date walking STD John Mayer circa 2009. When she came out of her teenage-girl-infatuated-with-brooding-guitar-player stupor, she wrote this song. Where do I begin? The opening Mayer-esque guitar licks…the searing vocals…the triumphant reminder that she’s not just a girl in a dress. She’s a songwriter. And rest assured, she’ll write your ass under the table if you break her heart.
2.Mine: “You made a rebel of a careless man’s careful daughter, You are the best thing that’s ever been mine.” YOU.MADE.A.REBEL…OF.A.CARELESS.MAN’S…CAREFUL.DAUGH.TER. This is the lyric Taylor tosses in to an upbeat, radio-friendly pop song. I have lain awake at night thinking about the genius of that lyric. This ranks number two for me because if you’re asking me the top examples of who she is as a songwriter, number one is a devastating ballad. Number two is a sparkly pop song that, created by any other artist, would have been fun but forgettable. When created by Taylor Swift, even the bubbliest pop song is packed with stunning lyrics.
1.All Too Well: In the Taylor Swift fandom, it’s downright cliché to rank this song as her best. But I just can’t help myself. I still remember the moment I first heard this song. I had been through a breakup the year before where the guy I was dating long distance broke up with me over the phone. I cried in my car as each lyric seemed to read my most intimate thoughts. “And you call me up again just to break me like a promise, so casually cruel in the name of being honest.” Though much ado has been made about the scarf featured in the song, that is not the point. (I swear if one more “journalist” asks Jake Gyllenhaal where the scarf is, I’m going to light something on fire.) The scarf is simply a metaphor for the little pieces of yourself you leave with someone in a relationship, and you never get those pieces back. Your mind races with memories, and the distance between those memories and the heartbreak you feel once the relationship ends can be devastating. But the triumph of Taylor Swift is that even in her sadness, she is empowered. “You can’t get rid of it, ‘cause you remember it all too well.” Swift knows she’s a lot to lose. And when you listen to this song, no matter how heartbroken you are, you know that you’re a lot to lose, too.
And that, reader, is her gift to us. Taylor Swift never runs from a Big Feeling. She embraces, embodies and magnifies what it’s like to feel without restraint. Are you sad? Great! Cry about it. Is there a bathroom floor nearby? Lie on it. Is it raining? So much the better. Have you fallen in love? How wonderful! How magical! Might I suggest kissing in the rain, having a pivotal conversation at 2:00 am, and feeling sure your love for this person is eternal despite having known them a literal day? That is, after all, what Taylor Swift would do. And God bless her for it. She’s become the soundtrack to so many of our lives by unapologetically living her life as an exposed nerve, acutely aware of the poetry of everyday life. And for that she will surely go down in history as one of the greatest songwriters of all time.